Electroreduction of optically active (
S)- and (
R)-
N-(3-butenyl)(or (
R)-
N-benzyl)-2-acetylpyrrolidines (
1a) and (
1b) (or (
2b)) were carried out in
N,
N-dimethylformamide containing Et
4NOTs as a supporting electrolyte, which brought about highly stereo- and regioselective intramolecular cyclization with diastereoselective asymmetric induction to give the corresponding (4
S,5
R,6
S)- and (4
R,5
S,6
R)-
cis-4,5-dimethyl-1-azabicyclo[4.3.0]nonan-5-ols (
3a) and (
3b) (or (8
R,9
S,10
R)-9-methyl-1-azatricycro[8.3.0
1,10.0
3,8]tridecane-9-ol-3,6-diene (
4b)) in 66% and 49% (or 31%) yields, respectively.
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